Multi-step reaction with 8 steps
1: 1.) 1.6 M butyl-lithium / 1.) hexane, THF, -6 to 0 deg C, 1 h, 2.) 0 deg C, 20 min
2: 65 percent / 10 percent v/v aq. hydrochloric acid / diethyl ether / 26 h / Ambient temperature
3: 1.) LDA / 1.) diethyl ether, -78 deg C, 45 min, 2.) diethyl ether, -78 deg C, 10 min
4: 92 percent Turnov. / di-isopropylamine, 4-(dimethylamino)pyridine / diethyl ether / 1.) 0 deg C, 30 min, 2.) room temperature, 40 h
5: 1.) ozone, 2.) triphenylphosphine / 1.) dichloromethane, -78 deg C, 1 min, 2.) --> room temperature, 3 h
6: 89 percent / potassium graphite, titanium trichloride / 1,2-dimethoxy-ethane / 1.) room temperature, 5 h, 2.) reflux, 5 h
7: 96 percent / 1.1 M tetrabutylammonium fluoride / tetrahydrofuran / 22 h / Ambient temperature
8: 97 percent / triethylamine / DMPA / CH2Cl2 / 24 h / Ambient temperature
With
hydrogenchloride; dmap; n-butyllithium; titanium(III) chloride; potassium graphite; tetrabutyl ammonium fluoride; ozone; triethylamine; diisopropylamine; triphenylphosphine; lithium diisopropyl amide;
0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane;